Upper Matecumbe Key Travel Guide
Tourist Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is £199 per night from 7 Jul to 8 Jul
£199
7 Jul - 8 Jul
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,725 reviews)
"This place was really nice and peaceful, I would book this place again! Also breakfast was really nice!"
Reviewed on 18 Jun 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is £233 per night from 16 Jul to 17 Jul
£233
16 Jul - 17 Jul
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
9.2/10 Wonderful! (1,317 reviews)
"We had a wonderful stay and really loved the resort. The room and balcony were absolutely perfect. My one suggestion would be to consider making one of the two beachfront pools adults-only. There is already an adults-only pool on the property, which is a nice option, but it’s located in the middle ..."
Reviewed on 15 Jun 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundable
The price is £294 per night from 13 Jul to 14 Jul
£294
13 Jul - 14 Jul
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,053 reviews)
"The resort was wonderful. Very clean. Very well laid out. The pools were never too crowded. The service was top notch. My favorite part was how beautiful the resort was. They must have spent a fortune on landscaping. My wife and I walked up and down the sea shore many of times and really enjoyed ..."
Reviewed on 18 Jun 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (698 reviews)
"First thing I noticed was how spotless the room was! I was impressed! Kudos to the cleaning staff. The kitchen was very well equipped with everything we could possibly need and the entire staff were super friendly and helpful! The pool is huge and there are plenty of seating choices both shaded and ..."
Reviewed on 17 Jun 2026
The Islands of Islamorada
82779 Old Hwy Islamorada FL
Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Florida Keys Brewing ...
9.6/10 Exceptional! (76 reviews)
"I am not usually about leaving reviews however this property definitely needs it. Heard a lot about being pampered when I was checked in and that they will bring you anything and to let them know what our needs were. Property does not have any coffee shop or restaurant. We were told we could come ..."
Reviewed on 18 May 2026
Oceanfront Private Cottage!
Islamorada FL
Stay at this cottage in Islamorada. Enjoy free Wi-Fi, patios and cable/satellite TV service. Popular attractions History of Diving Museum and Florida Keys Brewing ...
10/10 Exceptional! (117 reviews)
"Host was very responsive when we reached out and the place had everything we needed. The dock for the boat was very easy to get in and out of and we had plenty of room for the trailer. The place was also very clean."
Reviewed on 11 Jun 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Check Upper Matecumbe Key hotel availability
Stay near popular Upper Matecumbe Key attractions
Explore a world of travel with Expedia
- 4 Star Hotels in Islamorada
- 5 Star Hotels in Islamorada
- Hotels near Bud n' Mary's Dive Center
- Hotels near Florida Keys Brewing Co.
- Apartments in Islamorada
- B&B in Islamorada
- Adults Only Resorts & in Islamorada
- Aimbridge Hospitality Hotels in Islamorada
- Beach Resorts & in Islamorada
- Boutique Hotels in Islamorada
- Cheap Hotels in Islamorada
- Family-Friendly Hotels in Islamorada
- Gay-Friendly Hotels in Islamorada
- Golf Hotels in Islamorada
- Hilton Hotels in Islamorada
- Hotels Suites in Islamorada
- Hotels with a Bar in Islamorada
- Hotels with a View in Islamorada
- Hotels with Connecting Rooms in Islamorada
- Hotels with Early Check-in in Islamorada
- Hotels with Gym in Islamorada
- Hotels with Laundry Service in Islamorada
- Hotels with Hot Tubs in Islamorada
- Luxury Hotels in Islamorada
- Pet-Friendly Hotels in Islamorada
- Romantic Hotels in Islamorada
- Spa Hotels in Islamorada
- Hotels with Waterpark in Islamorada
- Wedding Hotels in Islamorada
- Yoga Hotels in Islamorada
- Islamorada Hotels
- Houseboats in Islamorada
- Motels in Islamorada
- Holiday Homes in Islamorada
- Villas in Islamorada
- Resorts in Lignumvitae Key Botanical State Park
- Lignumvitae Key Botanical State Park Hotels
- Holiday Homes in Lignumvitae Key Botanical State Park
- Apartments in Lower Matecumbe Key
- Condo Rentals in Lower Matecumbe Key
- Cottages in Lower Matecumbe Key
- Inns in Lower Matecumbe Key
- Matecumbe Hotels
- Riverside Hotels in Plantation Key
- Plantation Key Hotels
- Gay-Friendly Hotels in Seabreeze Trailer Park
- Venetian Shores Hotels
- Windley Key Hotels
- Visit Bahia Honda Key
- Visit Eden Pines
- Visit Big Pine Key
- Visit Big Torch Key
- Visit Cutler Bay
- Visit Duck Key
- Visit Elliott Key
- Visit Flamingo
- Visit Florida City
- Florida Keys Brewing Co.
- Visit Homestead
- Islamorada Holidays
- Visit Islamorada
- Visit Key Colony Beach
- Visit Anglers Park
- Visit Key Largo
- Visit Layton
- Visit Lignumvitae Key Botanical State Park
- Visit Little Torch Key
- Visit Long Key
- Visit Little Venice
- Visit Marathon
- Visit Kendall
- Visit Palmetto Bay
- Visit North Key Largo
- Visit Plantation Key
- Visit Princeton
- Visit Ramrod Key
- Visit Rock Harbor
- Visit Summerland Key
- Visit Tavernier
- Visit Tingler Island
- All inclusive Holiday Packages Lignumvitae Key Botanical State Park
- Ace Rental Cars in Windley Key
- Avis Rental Cars in Plantation Key
- Car hire Islamorada
- Discount Car Rentals Rental Cars in Lower Matecumbe Key
- Drive-A-Matic Rental Cars in Windley Key
- Goldcar Key’n Go Rental Cars in Windley Key
- Localiza Argentina Rental Cars in Windley Key
- Megadrive Rental Cars in Lower Matecumbe Key
- Record Rent A Car Rental Cars in Lower Matecumbe Key
- Rent A Wreck Rental Cars in Plantation Key
- Sixt Rental Cars in Plantation Key
- U-Save Rental Cars in Lower Matecumbe Key
